145356-39-4

Usage

Classification

Natural phenol

Occurrence

Found in various plants such as grapes, berries, and peanuts

Type of compound

Polyphenolic compound

Properties

Antioxidant

Potential health benefits

Anti-inflammatory and anti-cancer effects

Scientific interest

Numerous studies due to its potential role in promoting cardiovascular health and protecting against age-related diseases

Presence in red wine

Associated with the "French Paradox"

French Paradox

Observation that the French have a relatively low incidence of coronary heart disease despite consuming a diet high in saturated fats

Upstream product

• 263327-99-7 4,3’,4’-trimethoxystilbene 
• 3462-97-3 (4-methoxybenzyl)triphenylphosphonium bromide 
• 824-94-2 p-methoxybenzyl chloride 
• 18513-95-6 (E)-3,4,4'-trimethoxystilbene 
• 880354-47-2 (E)-1-(4'-acetoxyphenyl)-2-(3,4-dimethoxyphenyl)ethene 
• 2628-16-2 p-acetoxystyrene 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 10031-82-0 4-ethoxybenzaldehyde 
• 83459-29-4 (3,4-diethoxyphenyl)methanol 
• 27472-20-4 1,2-diethoxy-4-chloromethyl-benzene 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 128294-47-3 (E)-4-<2-(3,4-dimethoxyphenyl)ethenyl>phenol 

Downstream Products

• 952418-36-9 C₂₈H₂₂O₆ 

Relevant academic research and scientific papers

Direct injection gas chromatographic mass spectrometric assay for trans-resveratrol

We have developed a novel method to measure the concentration of the trihydroxystilbene trans-resveratrol suitable for the analysis of wine and other biological materials. Solid-phase extraction is carried out on a reversed-phase disposable C-18 cartridge

Discovery of trans-3,4,4′-trihydroxystilbene as new lead vasorelaxant agent for antihypertensive drug development

Aims: The structure-vasorelaxant activity relationships (SARs) assessment in previous study has found that trans-3,4,4′-trihydroxystilbene (344OH) could potentially act as a vasorelaxing agent with demonstration of over 2-fold maximal relaxation (Rmax) compared to its analogue, resveratrol. The present study focuses on the mechanism of actions and pathways employed by 344OH and compared to its analogue to further speculate the SAR of stilbenoids towards vasorelaxation. Materials and methods: The 344OH employed in present study was synthesized based on the protocol in previous study. The vascular responses towards the cumulative addition of 344OH were evaluated using in vitro rat aortic rings assays. Key findings: The pEC50 and Rmax values were found to be 4.33 ± 0.05 and 106 ± 3.99%, respectively. Results showed that the vasorelaxation of 344OH were predominated by G-protein-coupled muscarinic- (M3) and β2-adrenergic receptors, followed by PGI2/AC/cAMP- and NO/sGC/cGMP-dependent pathways. It was also identified that 344OH employed voltage-activated- (Kv), calcium-activated- (Kca) and inwardly-rectifying (Kir) potassium channels and act as an antagonist for both VOCC and IP3R while regulating the action potential in the vasculature. Significance: The different position of hydroxyl substituent located in A-ring of the stilbenoid backbone in 344OH compared to resveratrol resulted in a significant difference in mechanistic actions that lead to 344OH's fast-acting and less time-dependent vasorelaxation behaviour. This has substantially increased the potential of 344OH to be developed as an effective antihypertensive drug in future. Present findings further strengthen our inferences where the SARs study approach should be carried out as the mainstream methodology in future drug development research.

In vitro study and structure-activity relationship analysis of stilbenoid derivatives as powerful vasorelaxants: Discovery of new lead compound

The development of vasorelaxant as the antihypertensive drug is important as it produces a rapid and direct relaxation effect on the blood vessel muscles. Resveratrol (RV), as the most widely studied stilbenoid and the lead compound, inducing the excellent vasorelaxation effect through the multiple signalling pathways. In this study, the in vitro vascular response of the synthesized trans-stilbenoid derivatives, SB 1-8e were primarily evaluated by employing the phenylephrine (PE)-precontracted endothelium-intact isolated aortic rings. Herein we report trans-3,4,4′-trihydroxystilbene (SB 8b) exhibited surprisingly more than 2-fold improvement to the maximal relaxation (Rmax) of RV. This article also highlights the characterization of the aromatic protons in terms of their unique splitting patterns in 1H NMR.

Synthesis of resveratrol derivatives as new analgesic drugs through desensitization of the TRPA1 receptor

A series of 31 resveratrol derivatives was designed, synthesized and evaluated for activation and inhibition of the TRPA1 channel. Most acted as activators and desensitizers of TRPA1 channels like resveratrol or allyl isothiocyanate (AITC). Compound 4z (HUHS029) exhibited higher inhibitory activity than resveratrol with an IC50 value of 16.1?μM. The activity of 4z on TRPA1 was confirmed in TRPA1-expressing HEK293 cells, as well as in rat dorsal root ganglia neurons by a whole cell patch clamp recording. Furthermore, pretreatment with 4z exhibited an analgesic effect on AITC-evoked TRPA1-related pain behavior in vivo.

3. 4', 4 - three-stilbene esterification derivative and its preparation method and application (by machine translation)

The invention relates to 3, 4', 4 - three-stilbene ester derivatives, the general structural formula: , In the formula R1 , R2 , R3 Group can be selected from and One or several. The invention also relates to 3, 4', 4 - three-stilbene ester derivatives of the preparation method, the preparation method of the "three wastes" less, easy processing, as fungicide pesticide production compared to the environmental protection. The derivatives as a new fungicide applied to controlling plant diseases, can be applied to the resistance of pathogenic bacteria, effect, and has the advantage of low cost. (by machine translation)

A facile and rapid access to resveratrol derivatives and their radioprotective activity

A facile and rapid access to resveratrol derivatives has been achieved based on palladium-catalyzed oxidative Heck reaction of aryl boronic acids with styrenes followed by demethylation in moderate to good yields. A series of resveratrol derivatives with various functional groups has been synthesized easily. The radioprotective activity of synthesized compounds has also been evaluated using rat thymocytes. The results revealed that some resveratrol derivatives efficiently protected the thymocytes from radiation-induced apoptosis.

3,4,4′-Trihydroxy-trans-stilbene, an analogue of resveratrol, is a potent antioxidant and cytotoxic agent

Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a naturally occurring polyphenol widely distributed in food and dietary plants. This phytochemical has been intensively studied as an efficient antioxidant and anticancer agent, and a variety of substituted stilbenes have been developed in order to improve the potency of resveratrol. In this work, we described the synthesis of 3,4,4-trihydroxy-trans-stilbene (3,4,4′-THS), an analogue of resveratrol, and studied its antioxidant and cytotoxic activity in vitro. 3,4,4-THS was much more efficient than resveratrol in protecting against free radical-induced lipid peroxidation, photo-sensitized DNA oxidative damage, and free radical-induced hemolysis of human red blood cells. More potent growth inhibition in cultured human leukemia cells (HL-60) was also observed for 3,4,4-THS. The relationship between the antioxidant efficiency and cytotoxic activity was discussed, with the emphasis on inhibition of the free radical enzyme ribonucleotide reductase by antioxidants. The result that this subtle structure modification of resveratrol drastically improves its bioactivity provides important strategy to develop novel resveratrol-based molecules.

Antioxidant-based lead discovery for cancer chemoprevention: the case of resveratrol

Resveratrol is a well-known natural antioxidant and cancer chemopreventive agent that has attracted much nterest in the past decade. Resveratrol-directed compounds were synthesized, and their antioxidant effects gainst reactive oxygen species (ROS)-induced DNA damage, their prooxidant effects on DNA damage in he presence cupric ions, and their cytotoxic and apoptosis-inducing effects on human promyelocytic leukemia(HL-60) cells were investigated in vitro. It was found that the compounds bearing o-diphenoxyl groups exhibited remarkably higher activities in inhibiting ROS-induced DNA damage, accelerating DNA damage in the presence cupric ions, and inducing apoptosis of HL-60 cells compared with the ones bearing no such groups. The detail mechanism of the structure-activity relationship was also studied by the oxidative product analysis of resveratrol and its analogues with galvinoxyl radical or cupric ions and UV-visible spectra change in the presence cupric ions. This study reveals a good and interesting correlation between antioxidant and prooxidant activity, as well as cytotoxicity and apoptosis-inducing activity against HL-60 cells, and provides an idea for designing antioxidant-based cancer chemoprevention agents. ?2009 American Chemical Society.

Hydroxystilbene compounds for reducing/inhibiting protein glycation

The hydroxystilbenes are well suited for reducing or inhibiting the glycation of certain substrates, for example the proteins of nails and/or hair, advantageously to preventatively and/or curatively combat glycation-related aging of the nails/hair.

Synthesis and Protein-Tyrosine Kinase Inhibitory Activity of Polyhydroxylated Stilbene Analogues of Piceatannol

A series of hydroxylated trans-stilbene related to the antileukemic natural product trans-3,3',4,5'-tetrahydroxy stilbene (piceatannol) (1) has been prepared and tested for inhibition of the lymphoid cell lineage-specific protein-tyrosine kinase p56lck, which plays an important role in lymphocyte proliferation and immune function.A number of the analogues displayed enhanced enzyme inhibitory activity relative to the natural product.Reduction of the double bond bridging the two aromatic rings and benzylation of the phenolic hydroxyl groups was found to decrease activity significantly.The most potent compounds in the series proved to be trans-3,3',5,5'-tetrahydroxystilbene, trans-3,3',5-trihydroxystilbene, and trans-3,4,4'-trihydroxystilbene.